1213855-60-7

Basic information

• Product Name: Boc-4-bromo-D-phenylalanine methyl ester
• Synonyms: Boc-4-bromo-D-phenylalanine methyl ester;D-Phenylalanine, 4-bromo-N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester;methyl (R)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate;N-BOC-P-BROMO-D-PHENYLALANINE METHYL ESTER
• CAS NO: 1213855-60-7
• Molecular Formula: C₁₅H₂₀BrNO₄
• Molecular Weight: 358.2276
• Mol File: 1213855-60-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Boc-4-bromo-D-phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-4-bromo-D-phenylalanine methyl ester(1213855-60-7)
• EPA Substance Registry System: Boc-4-bromo-D-phenylalanine methyl ester(1213855-60-7)

Safety Data

• Hazardous Substances Data: 1213855-60-7(Hazardous Substances Data)

Usage

General Description

Boc-4-bromo-D-phenylalanine methyl ester is a chemical compound that is a derivative of the amino acid phenylalanine. It has a Boc (tert-butoxycarbonyl) protecting group, a bromine atom, and a methyl ester group attached to the phenylalanine molecule. Boc-4-bromo-D-phenylalanine methyl ester is often used in peptide synthesis and pharmaceutical research as a building block for creating peptide-based drugs and therapeutics. It is important to handle this compound with care and proper safety precautions, as it is a potentially hazardous chemical.

Upstream product

• 1155375-46-4 (Z)-methyl 3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)acrylate 
• 76757-90-9 N-(tert-butoxycarbonyl)-D-tyrosine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 122332-24-5 (R)-methyl 2-amino-3-(4-bromophenyl)propanoate 
• 62561-74-4 (2R)-2-amino-3-(4-bromophenyl)propanoic acid 
• 459133-43-8 (R)-2-amino-3-(4-bromophenyl)propionic acid methyl ester hydrochloride 
• 79561-82-3 (2R)-3-(4-bromophenyl)-2-[[(tert-butoxy)carbonyl]amino]propanoic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 79561-82-3 (2R)-3-(4-bromophenyl)-2-[[(tert-butoxy)carbonyl]amino]propanoic acid 
• 1246363-08-5 tert-butyl [(2R)-1-(4-bromophenyl)-3-oxypropan-2-yl] carbamate 
• 149818-98-4 methyl (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanoate 
• 1426129-50-1 N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester 
• 149709-58-0 (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal 
• 149709-59-1 ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate 
• 1012341-48-8 (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid 
• 1012341-50-2 (2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid 
• 335030-24-5 methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 

Relevant articles and documents

Preparation method of sacubitril intermediate

The invention relates to the technical field of synthesis of medical intermediates, in particular to a preparation method of a sacubitril intermediate, which comprises the following steps: 1) reacting a raw material compound III with phosphorus trihalide to obtain a compound II; and 2) reacting the compound II with phenylhydrazine in the presence of a catalyst and an additive to obtain a sacubitril intermediate, namely a compound I. According to the invention, cheap phosphorus trihalide is selected to replace expensive and highly toxic trifluoromethanesulfonic anhydride, and cheap phenylhydrazine and a catalyst palladium chloride are adopted. The method has the advantages of simple reaction operation, low cost and high yield, and is easier for industrial production of the compound I.

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The invention discloses a method for synthesizing an AHU377 calcium salt. The method comprises the following steps: reacting 4-bromo-D-phenylalanine with thionyl chloride, reacting obtained methyl 4-bromo-D-phenylalaninate hydrochloride with BOC acid anhydride, reacting the obtained reaction product with phenylmagnesium bromide to obtain N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methylester, reacting the N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methyl ester with sodium borohydride, reacting the obtained reaction product with ethyl 2-(triphenylphosphoranylidene)propionate to obtain ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoate, reacting the ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoatewith lithium hydroxide, performing catalytic hydrogenation, reacting the obtained catalytic hydrogenation product with thionyl chloride to obtain ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, and stirring and reacting the ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, calcium chloride and succinic anhydride to obtain the target product.The method has the advantages of simple steps, mild reaction conditions, high purity and high yield.

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